
TY  - JOUR
A1  - Norton, AK 
A1  - Vonitzstein, M 
T1  - The Synthesis of 6-Substituted Methyl 1-O-Acetyl-3,4-anhydro-&#946;-D-Tagatofuranosides. Regioselective Chlorination and Thioacetylation in the Presence of an Oxiran
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 3
SP  - 281
EP  - 283
KW  - 
UR  - https://doi.org/10.1071/CH9960281 
N2  - Methyl 1-O-acetyl-6-S-acetyl-3,4-anhydro-6-thio-&#946;-D-tagatofuranoside (the 1-acetate of (2)) and methyl 1-O-acetyl-3,4-anhydro-6-chloro-6-deoxy-&#946;-D-tagatofuranoside (the 1-acetate of (3)) have been prepared as fructose derivatives by treatment of methyl 3,4-anhydro-&#946;-D-tagatofuranoside (1) with (p-dimethylaminophenyl ) diphenylphosphine/diisopropyl azodicarboxylate/thioacetic S-acid and (p- dimethylaminophenyl ) diphenylphosphine/tetrachloromethane respectively. The reactions proceed in good yield, under mild conditions, and are selective for the 6-hydroxy group. The oxiran ring is unaffected under these conditions. 
ER  -

